Book Holiday Homes in Oswego

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Featured Holiday Homes in Oswego

Geneva Island Park Retreat

Geneva Island Park Retreat

Geneva
With a stay at this vacation home in Geneva, you'll be within a 15-minute walk of Island Park and C'est La Vie.
Geneva Island Park Retreat
Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.

Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.

Aurora
The price is AU$1,520 per night from 17 Mar to 18 Mar
AU$1,520
includes taxes & fees
17 Mar - 18 Mar
When you stay at this vacation home in Aurora, you'll be within a 10-minute drive of Aurora Regional Fire Museum and Hollywood Casino Aurora.
Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall.
Furnished Private home in Aurora sleeps 9 guests

Furnished Private home in Aurora sleeps 9 guests

Aurora
Located in Aurora, this vacation home is within a 5-minute drive of Copley Memorial Hospital and Rush-Copley Medical Center.
Furnished Private home in Aurora sleeps 9 guests
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Cozy 5-bedroom with lake views and spacious deck

Cozy 5-bedroom with lake views and spacious deck

Westmont
Located in Westmont, this vacation home is on a lake, within a 5-minute drive of Ty Warner Park and Graue Mill and Museum.
Cozy 5-bedroom with lake views and spacious deck
- Fully-Equipped Condo - King Bed - Massive yard -

- Fully-Equipped Condo - King Bed - Massive yard -

Geneva
The price is AU$514 per night from 23 Mar to 24 Mar
AU$514
includes taxes & fees
23 Mar - 24 Mar
Located in Geneva, this vacation home is within a 15-minute walk of C'est La Vie and Geneva History Center.
- Fully-Equipped Condo - King Bed - Massive yard -
Elegant Getaway near Oakbrook Mall 20 min dtwn CHI

Elegant Getaway near Oakbrook Mall 20 min dtwn CHI

Westmont
Located in Westmont, this vacation home is within a 5-minute drive of Ty Warner Park and Mayslake Peabody Mansion.
Elegant Getaway near Oakbrook Mall 20 min dtwn CHI
OutdoorOasis-King bed-Fire Pit-Mins to town-EV charger

OutdoorOasis-King bed-Fire Pit-Mins to town-EV charger

Geneva
With a stay at this vacation home in Geneva, you'll be within a 5-minute drive of Island Park and C'est La Vie.
OutdoorOasis-King bed-Fire Pit-Mins to town-EV charger
✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station

Wheaton
The price is AU$460 per night from 24 Mar to 25 Mar
AU$460
includes taxes & fees
24 Mar - 25 Mar
With a stay at this vacation home in Wheaton, you'll be within a 5-minute drive of Wheaton College and Billy Graham Center Museum.
✽ Charming Cottage ✽ close to College/Town/Station
Spacious open concept home w/ game room + firepit

Spacious open concept home w/ game room + firepit

Winfield
With a stay at this vacation home in Winfield, you'll be within a 5-minute drive of Cosley Zoo and Central Dupage Hospital.
Spacious open concept home w/ game room + firepit
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Oswego Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Oswego vacation homes are the perfect way for you to wing it.

Holiday houses in Oswego let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Oswego in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Oswego adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Oswego with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Oswego vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Oswego Holiday Homes essential information

Accommodation
143 Holiday Homes
Lowest Price
AU$94
Highest Price
AU$1,520
Popular accommodation
Geneva Island Park Retreat, Spacious and family friendly getaway. 8 mins from Chicago Premium Outlet Mall. , Furnished Private home in Aurora sleeps 9 guests, Cozy 5-bedroom with lake views and spacious deck, - Fully-Equipped Condo - King Bed - Massive yard -, Elegant Getaway near Oakbrook Mall 20 min dtwn CHI , OutdoorOasis-King bed-Fire Pit-Mins to town-EV charger, ✽ Charming Cottage ✽ close to College/Town/Station, Spacious open concept home w/ game room + firepit

Top trending hotels in Oswego

SureStay Plus Hotel by Best Western Chicago Lombard

SureStay Plus Hotel by Best Western Chicago Lombard

2.5 out of 5
222 E 22nd Street, Lombard, IL
Fully refundableReserve now, pay when you stay
The price is AU$134 per night from 17 Mar to 18 Mar
AU$134
includes taxes & fees
17 Mar - 18 Mar
Located in Lombard (Highland Hills), SureStay Plus Hotel by Best Western Chicago Lombard is within a 5-minute drive of Yorktown Shopping Center and Advocate ...
SureStay Plus Hotel by Best Western Chicago Lombard
The Champagne Lodge & Luxury Suites

The Champagne Lodge & Luxury Suites

3.5 out of 5
16 W 621 S. Frontage Rd, Willowbrook, IL
The price is AU$199 per night from 17 Mar to 18 Mar
AU$199
includes taxes & fees
17 Mar - 18 Mar
Located in Willowbrook, The Champagne Lodge & Luxury Suites is a 4-minute drive from Willowbrook Community Park and 6 minutes from Burr Ridge Village ...
The Champagne Lodge & Luxury Suites
Red Roof Inn Chicago - Joliet

Red Roof Inn Chicago - Joliet

2 out of 5
1750 Mcdonough St, Joliet, IL
Fully refundableReserve now, pay when you stay
The price is AU$94 per night from 17 Mar to 18 Mar
AU$94
includes taxes & fees
17 Mar - 18 Mar
With a stay at Red Roof Inn Chicago - Joliet in Joliet, you'll be within a 10-minute drive of Harrah's Casino and Route 66 Raceway.
Red Roof Inn Chicago - Joliet
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Chicago Club Inn & Suites

Chicago Club Inn & Suites

3 out of 5
630 Pasquinelli Dr, Westmont, IL
Fully refundableReserve now, pay when you stay
The price is AU$119 per night from 15 Apr to 16 Apr
AU$119
includes taxes & fees
15 Apr - 16 Apr
Located in Westmont, Chicago Club Inn & Suites is in the suburbs, within a 10-minute drive of Oakbrook Center Mall and Yorktown Shopping Center.
Chicago Club Inn & Suites
Don't see what you're looking for?
See all available properties in Oswego
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.